Windward Islands Vacation Packages
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Price found within the past 48 hours. Click for updated prices.
3.0-star property
Big Bear Spa Suites
8.2/10 Very Good! (350 reviews)
Dec 20 - Dec 27
7 night stay
Dallas (DFW) to Los Angeles (LAX)
Frontier Airlines • Roundtrip • Coach
Price was $5,745, price is now $2,318 per person
$2,318
per person
found 1 day ago
This place was so comfy and cozy, the bed was so comfortable and the spa in the room was amazing. We loved it and will definitely stay here again.
Reviewed on Oct 7, 2026
5.0-star property
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
8/10 Very Good! (1 review)
Dec 26 - Jan 2
7 night stay
Chicago (ORD) to Miami (MIA)
United • Roundtrip • Coach
Price was $59,715, price is now $28,265 per person
$28,265
per person
found 1 day ago
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....
Reviewed on Jun 22, 2016
3.5-star property
Broadway Suites Downtown by RocketStay
Coral Way
8.6/10 Excellent! (229 reviews)
Jan 1 - Jan 9
8 night stay
San Juan (SJU) to Miami (MIA)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,178, price is now $1,094 per person
$1,094
per person
found 1 day ago
Muy bien ubicado, limpio, buena relación precio calidad
Reviewed on Aug 9, 2026
Top rated hotels for your Windward Islands vacation package
Siesta Hotel
Morne Rouge Street St. George's
106.61 mi from city center
$96 nightly
The price is $107 total per night
$107 total
Nov 13 - Nov 14
Total with taxes and fees
Guests of Siesta Hotel enjoy features like an outdoor pool, free WiFi in public areas, and a terrace. There's free parking, and an airport shuttle (available 24 hours) for USD 20 per vehicle one-way. Front-desk staff can assist with securing valuables, luggage storage, and concierge services. This family-friendly hotel also has a garden.
Pool
Parking included
Secrets St. Lucia Resort & Spa All Inclusive Adults Only
1 Choc Bay Gros Islet
Free Cancellation
Reserve now, pay when you stay
42.98 mi from city center
$799 nightly
The price is $799 total per night
$799 total
Oct 17 - Oct 18
Total with taxes and fees
Secrets St. Lucia Resort & Spa All Inclusive Adults Only features a private beach, a full-service spa, and 3 outdoor pools. A stay here includes free parking. The front desk has multilingual staff on hand 24/7 to help with luggage storage, securing valuables, and concierge services. Additional amenities include karaoke, a 24-hour gym, and a sauna.
On private beach
Pool
Coconut Bay Beach Resort & Spa All Inclusive
Eau Piquant Vieux Fort
27.58 mi from city center
Coconut Bay Beach Resort & Spa All Inclusive features a full-service spa, 5 outdoor pools, and a free water park. There's free parking, as well as a free airport shuttle (available 24 hours). The 24-hour front desk has staff standing by to help with tours/tickets and dry cleaning/laundry. Additional amenities include a nightclub, a lazy river, and a children's pool.
Pool
All inclusive
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View all propertiesLowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
